CA2422582C - Combinations of active ingredients for protecting animal skins and leather - Google Patents
Combinations of active ingredients for protecting animal skins and leather Download PDFInfo
- Publication number
- CA2422582C CA2422582C CA2422582A CA2422582A CA2422582C CA 2422582 C CA2422582 C CA 2422582C CA 2422582 A CA2422582 A CA 2422582A CA 2422582 A CA2422582 A CA 2422582A CA 2422582 C CA2422582 C CA 2422582C
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- Prior art keywords
- cmk
- leather
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- combinations
- chlorophenol
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- C—CHEMISTRY; METALLURGY
- C14—SKINS; HIDES; PELTS; LEATHER
- C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
- C14C9/00—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
-
- C—CHEMISTRY; METALLURGY
- C14—SKINS; HIDES; PELTS; LEATHER
- C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
- C14C1/00—Chemical treatment prior to tanning
- C14C1/02—Curing raw hides
Abstract
The invention relates to the use of combinations of active ingredients, containing phenolic and fungicidal active ingredients, for preserving animal skins and leather.
Description
COMBINATIONS OF ACTIVE INGREDIENTS
FOR PROTECTING ANIMAL SKINS AND LEATHER
The present application relates to the use of active compound. combinations containing phenolic active compounds and fungicidal active compounds for preserving animal hides and leather.
It is known that phenol derivatives and mixtures or formulations thereof can be used as compositions for the protection of materials in leather manufacture.
However, it has emerged that these compounds, when employed alone or in combination, do not offer sufficient protection of stored hides and leather against microbial attack after some time.
It is furthermore known that benzimidazoles, imidazoles, triazoles and/or morpholine derivatives in combination with phenolic compounds make possible a protection of the animal hides and leather during manufacture and storage (US 5 888 415).
The use of 2-mercaptopyridine N-oxide and its salts for preserving leather - is also known (WO 98/56959).
- la -In one aspect, the invention provides a mixture, comprising: (a) at least one fungicidal compound selected from the group consisting of mercaptobenzothiazole, benzisothiazolinone, octylisothiazolinone and dichlorooctylisothiazolinone; and (b) two or more phenolic compounds selected from the group consisting of 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4-chlorophenol, and an ammonium, alkali metal and alkaline earth metal salt thereof.
In a further aspect, the invention provides a method of protecting an animal hide or leather from microbial attack, comprising treating the hide or leather with a mixture as defined above.
In a still further aspect, the invention provides a microbicidal composition comprising a mixture as defined above.
Surprisingly, it has now been found that combinations of certain fungicidal reactive active compounds such as mercaptobenzothiazole, methylene bisthiocyanate, thiocyanomethylthiobenzothiazole (TCMTB), benzisothiazolinone (BIT), octylisothiazolinone (OIT), dichlorooctylisothiazolinone (DCOIT), chiorothalonil, iodopropinyl butylcarbamate (IPBC), di-iodomethyl p-tolyl sulphone, N-cyclohexylbenzothiophene-2-carboxamide 5,5-dioxide and dithio-2,2'-bisbenzylmethylamide and specific phenolic active compounds are outstandingly suitable for the preservation of animal hides and leather.
Suitable phenolic active compounds are preferably phenol derivatives such as tribromophenol, tricholophenol, nitrophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophene, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4-chlorophenol (chlorophene), 2,4-dichloro-3,5-dimethylphenol, 4-chlorothymol, triclosan, fentichlor and their ammonium, alkali metal and alkaline earth metal salts, and mixtures of these.
Preferred are combinations containing 3,5-dimethyl-4-chlorophenol, 2-benzyl-4-chlorophenol (BP), 3-methyl-4-chlorophenol (CMK) and/or o-phenylphenol (OPP) as phenolic constituents and one or more of the abovementioned fungicides.
The following combinations may be mentioned in particular:
CMK/mercaptobenzothiazole CMK/methylene bisthiocyanate CMK/thiocyanomethylthiobenzothiazole (TCMTB) CMK/benzisothiazolinone (BIT) CMK/octylisothiazolinone (OIT) CMK/dichlorooctylisothiazolinone (DCOIT) CMK/iodopropinyl butylcarbamate (IPBC) CMK/di-iodomethyl p-tolyl sulphone CMK/N-cyclohexylbenzothiophene-2-carboxamide S,S-dioxide OPP/mercaptobenzothiazole OPP/methylene bisthiocyanate OPP/thiocyanomethylthiobenzothiazole (TCMTB) OPP/benzisothiazolinone (BIT) OPP/octylisothiazolinone (OTT) OPP/dichlorooctylisothiazolinone (DCOIT) OPP/iodopropinyl butylcarbamate (IPBC) OPP/di-iodomethyl p-tolyl sulphone OPP/N-cyclohexylbenzothiophene-2-carboxamide S,S-dioxide CMK/OPP/mercaptobenzothiazole CMK/OPP/m ethylene bisthiocyanate CMK/OPP/thiocyanomethylthiobenzothiazole. (TCMTB) CMK/OPP/benzisothiazolinone (BIT) CMK/OPP/octylisothiazolinone (OIT) CMK/OPP/dichlorooctylisothiazolinone (DCOIT) CMK/OPP/iodopropinyl butylcarbamate (IPBC) CMK/OPP/di-iodomethyl p-tolyl sulphone CMK/OPP/N-cyclohexylbenzothiophene-2-carboxamide S,S-dioxide CMK/BP/mercaptobenzothiazole CMK/BP/methylene bisthiocyanate CMK/BP/thiocyanomethylthiobenzothiazole (TCMTB) CMK/BP/benzisothiazolinone (BIT) CMK/BP/octylisothiazolinone (OIT) CMK/BP/dichlorooctylisothiazolinone (DCOIT) CMK/BP/iodopropinyl butylcarbamate (IPBC) CMK/BP/di-iodomethyl p-tolyl sulphone CMK/BP/N-cyclohexylbenzothiophene-2-carboxamide S,S-dioxide The abovementioned fungicidal and phenolic compounds are known, see, for example, "Microbicides for the Protection of Materials, Chapmann & Hall, 1993".
In general, 5 to 200, preferably 10 to 100 and especially preferably 12 to 50 parts by weight of one or more of the abovementioned phenolic compounds are employed per part by weight of one or more of the abovementioned fungicides in the combinations.
If two or more phenolic compounds are present in the combinations according to the invention, their ratio to each other can be varied within wide limits.
Advantageous ratios can be determined in a simple fashion by conventional experiments which are known to the skilled worker.
As a rule, the weight ratio between two phenolic compounds is between 1:1 and 1:10.
If, for example, OPP is present in addition to CMK in a combination according to the invention, the preferred weight ratio OPP:CMK is between 1:1 and 1:5.
FOR PROTECTING ANIMAL SKINS AND LEATHER
The present application relates to the use of active compound. combinations containing phenolic active compounds and fungicidal active compounds for preserving animal hides and leather.
It is known that phenol derivatives and mixtures or formulations thereof can be used as compositions for the protection of materials in leather manufacture.
However, it has emerged that these compounds, when employed alone or in combination, do not offer sufficient protection of stored hides and leather against microbial attack after some time.
It is furthermore known that benzimidazoles, imidazoles, triazoles and/or morpholine derivatives in combination with phenolic compounds make possible a protection of the animal hides and leather during manufacture and storage (US 5 888 415).
The use of 2-mercaptopyridine N-oxide and its salts for preserving leather - is also known (WO 98/56959).
- la -In one aspect, the invention provides a mixture, comprising: (a) at least one fungicidal compound selected from the group consisting of mercaptobenzothiazole, benzisothiazolinone, octylisothiazolinone and dichlorooctylisothiazolinone; and (b) two or more phenolic compounds selected from the group consisting of 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4-chlorophenol, and an ammonium, alkali metal and alkaline earth metal salt thereof.
In a further aspect, the invention provides a method of protecting an animal hide or leather from microbial attack, comprising treating the hide or leather with a mixture as defined above.
In a still further aspect, the invention provides a microbicidal composition comprising a mixture as defined above.
Surprisingly, it has now been found that combinations of certain fungicidal reactive active compounds such as mercaptobenzothiazole, methylene bisthiocyanate, thiocyanomethylthiobenzothiazole (TCMTB), benzisothiazolinone (BIT), octylisothiazolinone (OIT), dichlorooctylisothiazolinone (DCOIT), chiorothalonil, iodopropinyl butylcarbamate (IPBC), di-iodomethyl p-tolyl sulphone, N-cyclohexylbenzothiophene-2-carboxamide 5,5-dioxide and dithio-2,2'-bisbenzylmethylamide and specific phenolic active compounds are outstandingly suitable for the preservation of animal hides and leather.
Suitable phenolic active compounds are preferably phenol derivatives such as tribromophenol, tricholophenol, nitrophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophene, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4-chlorophenol (chlorophene), 2,4-dichloro-3,5-dimethylphenol, 4-chlorothymol, triclosan, fentichlor and their ammonium, alkali metal and alkaline earth metal salts, and mixtures of these.
Preferred are combinations containing 3,5-dimethyl-4-chlorophenol, 2-benzyl-4-chlorophenol (BP), 3-methyl-4-chlorophenol (CMK) and/or o-phenylphenol (OPP) as phenolic constituents and one or more of the abovementioned fungicides.
The following combinations may be mentioned in particular:
CMK/mercaptobenzothiazole CMK/methylene bisthiocyanate CMK/thiocyanomethylthiobenzothiazole (TCMTB) CMK/benzisothiazolinone (BIT) CMK/octylisothiazolinone (OIT) CMK/dichlorooctylisothiazolinone (DCOIT) CMK/iodopropinyl butylcarbamate (IPBC) CMK/di-iodomethyl p-tolyl sulphone CMK/N-cyclohexylbenzothiophene-2-carboxamide S,S-dioxide OPP/mercaptobenzothiazole OPP/methylene bisthiocyanate OPP/thiocyanomethylthiobenzothiazole (TCMTB) OPP/benzisothiazolinone (BIT) OPP/octylisothiazolinone (OTT) OPP/dichlorooctylisothiazolinone (DCOIT) OPP/iodopropinyl butylcarbamate (IPBC) OPP/di-iodomethyl p-tolyl sulphone OPP/N-cyclohexylbenzothiophene-2-carboxamide S,S-dioxide CMK/OPP/mercaptobenzothiazole CMK/OPP/m ethylene bisthiocyanate CMK/OPP/thiocyanomethylthiobenzothiazole. (TCMTB) CMK/OPP/benzisothiazolinone (BIT) CMK/OPP/octylisothiazolinone (OIT) CMK/OPP/dichlorooctylisothiazolinone (DCOIT) CMK/OPP/iodopropinyl butylcarbamate (IPBC) CMK/OPP/di-iodomethyl p-tolyl sulphone CMK/OPP/N-cyclohexylbenzothiophene-2-carboxamide S,S-dioxide CMK/BP/mercaptobenzothiazole CMK/BP/methylene bisthiocyanate CMK/BP/thiocyanomethylthiobenzothiazole (TCMTB) CMK/BP/benzisothiazolinone (BIT) CMK/BP/octylisothiazolinone (OIT) CMK/BP/dichlorooctylisothiazolinone (DCOIT) CMK/BP/iodopropinyl butylcarbamate (IPBC) CMK/BP/di-iodomethyl p-tolyl sulphone CMK/BP/N-cyclohexylbenzothiophene-2-carboxamide S,S-dioxide The abovementioned fungicidal and phenolic compounds are known, see, for example, "Microbicides for the Protection of Materials, Chapmann & Hall, 1993".
In general, 5 to 200, preferably 10 to 100 and especially preferably 12 to 50 parts by weight of one or more of the abovementioned phenolic compounds are employed per part by weight of one or more of the abovementioned fungicides in the combinations.
If two or more phenolic compounds are present in the combinations according to the invention, their ratio to each other can be varied within wide limits.
Advantageous ratios can be determined in a simple fashion by conventional experiments which are known to the skilled worker.
As a rule, the weight ratio between two phenolic compounds is between 1:1 and 1:10.
If, for example, OPP is present in addition to CMK in a combination according to the invention, the preferred weight ratio OPP:CMK is between 1:1 and 1:5.
Surprisingly, the combinations according to the invention have a synergistic action, that is to say the action of the combination exceeds the action of the individual active compounds.
In general, the combinations according to the invention of the active compounds are employed in the form of formulations. The use concentration is preferably 0.1 to I%
of active compound or active compound mixture based on the hides or leather to be protected.
The compositions arising from the formulation contain the active compound mixture preferably in an amount of 10 to 50%. In general, the compositions contain the following as further constituents: 0 to 30% alkali metal and/or alkaline earth metal hydroxides; 0 to 20% ionic and/or nonionic emulsifiers; 5 to 60% organic solvents such as, in particular, glycols, ketones, glycol ethers, alcohols such as ethanol, methanol, 1,2-propanediol, n-propanol and 0 to 0.5% of odoriferous substances and fragrances. The remainder to 100% is water or organic solvent, such as, for example, 1,2-propanediol. The percentages stated are by weight.
The active compound mixtures and the compositions which can be prepared from them are used in accordance with the invention by generally customary application methods in leather manufacture for the protection of animal hides against attack and damage by microorganisms. It is of particular interest in this context that representatives of the species Aspergillus niger, Aspergillus repens, Hormoconis resinae, Penicillium glaucum and Trichoderma viride, Penicillium species such as P. citrinum or P. glaucum, Paecilomyces variotii, Cladosporium species and Mucor species such as Mucor mucedo, Rhizopus species such as Rhizopus oryzae, Thizopus rouxii are suppressed fully and permanently.
The examples which follow are intended to illustrate the invention and are not limited thereto.
In general, the combinations according to the invention of the active compounds are employed in the form of formulations. The use concentration is preferably 0.1 to I%
of active compound or active compound mixture based on the hides or leather to be protected.
The compositions arising from the formulation contain the active compound mixture preferably in an amount of 10 to 50%. In general, the compositions contain the following as further constituents: 0 to 30% alkali metal and/or alkaline earth metal hydroxides; 0 to 20% ionic and/or nonionic emulsifiers; 5 to 60% organic solvents such as, in particular, glycols, ketones, glycol ethers, alcohols such as ethanol, methanol, 1,2-propanediol, n-propanol and 0 to 0.5% of odoriferous substances and fragrances. The remainder to 100% is water or organic solvent, such as, for example, 1,2-propanediol. The percentages stated are by weight.
The active compound mixtures and the compositions which can be prepared from them are used in accordance with the invention by generally customary application methods in leather manufacture for the protection of animal hides against attack and damage by microorganisms. It is of particular interest in this context that representatives of the species Aspergillus niger, Aspergillus repens, Hormoconis resinae, Penicillium glaucum and Trichoderma viride, Penicillium species such as P. citrinum or P. glaucum, Paecilomyces variotii, Cladosporium species and Mucor species such as Mucor mucedo, Rhizopus species such as Rhizopus oryzae, Thizopus rouxii are suppressed fully and permanently.
The examples which follow are intended to illustrate the invention and are not limited thereto.
Example 1 Agar plates are inoculated with conidia of the species Aspergillus niger, Aspergillus repens, Penicillium glaucum, Trichoderma viride and Hormoconis resinae. Wet blue samples treated with mixture I, II and mixture III are then placed on the agar plates and incubated for 28 days at 20 to 30 C and a relative atmospheric humidity of 95%.
Mixture I Mixture II
30 parts by weight of p-chloro-m-cresol 10.parts by weight of octylisothiazolinone 13 parts by weight of o-phenylphenol Mixture III
30 parts by weight of p-chloro-m-cresol 10 parts by weight of 2-benzyl-4-chlorophenol 2 parts by weight of octylisothiazolinone Mould growth is observed on the test pieces after an incubation time of as little as 10 days in the case of the wet blues preserved with mixture I and mixture U.
No growth is observed after an incubation time of 20 days in the case of mixture III.
Example 2 Formulation I Formulation II
parts by weight of p-chloro-m-cresol 2-/ parts by weight of p-chloro-m-cresol 13 parts by weight of o-phenylphenol 12 parts by weight of 2-benzyl-4-chlorophenol 2 parts by weight of octylisothiazolinone 1 part by weight of octylisothiazolinone 12 parts by weight of NaOH Remainder to 100 parts by weight :
1,2-propanediol 14 parts by weight of 1,2-propanediol Remainder to 100 parts by weight: water
Mixture I Mixture II
30 parts by weight of p-chloro-m-cresol 10.parts by weight of octylisothiazolinone 13 parts by weight of o-phenylphenol Mixture III
30 parts by weight of p-chloro-m-cresol 10 parts by weight of 2-benzyl-4-chlorophenol 2 parts by weight of octylisothiazolinone Mould growth is observed on the test pieces after an incubation time of as little as 10 days in the case of the wet blues preserved with mixture I and mixture U.
No growth is observed after an incubation time of 20 days in the case of mixture III.
Example 2 Formulation I Formulation II
parts by weight of p-chloro-m-cresol 2-/ parts by weight of p-chloro-m-cresol 13 parts by weight of o-phenylphenol 12 parts by weight of 2-benzyl-4-chlorophenol 2 parts by weight of octylisothiazolinone 1 part by weight of octylisothiazolinone 12 parts by weight of NaOH Remainder to 100 parts by weight :
1,2-propanediol 14 parts by weight of 1,2-propanediol Remainder to 100 parts by weight: water
Claims
1. A mixture, comprising:
(a) at least one fungicidal compound selected from the group consisting of mercaptobenzothiazole, benzisothiazolinone, octylisothiazolinone and dichlorooctylisothiazolinone; and (b) two or more phenolic compounds selected from the group consisting of 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4-chlorophenol, and an ammonium, alkali metal and alkaline earth metal salt thereof.
2. A method of protecting an animal hide or leather from microbial attack, comprising treating the hide or leather with a mixture according to claim 1.
3. A microbicidal composition comprising a mixture according to
claim 1.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10046265A DE10046265A1 (en) | 2000-09-19 | 2000-09-19 | Synergistic mixtures protecting animal hides or leather against microbial attack comprise phenols and fungicides such as mercaptobenzothiazole or chlorthalonil |
| DE10046265.0 | 2000-09-19 | ||
| PCT/EP2001/010303 WO2002023985A2 (en) | 2000-09-19 | 2001-09-07 | Combinations of active ingredients for protecting animal skins and leather |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2422582A1 CA2422582A1 (en) | 2003-03-14 |
| CA2422582C true CA2422582C (en) | 2011-11-29 |
Family
ID=7656740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2422582A Expired - Fee Related CA2422582C (en) | 2000-09-19 | 2001-09-07 | Combinations of active ingredients for protecting animal skins and leather |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7201854B2 (en) |
| EP (1) | EP1328155B1 (en) |
| JP (1) | JP2004509137A (en) |
| KR (1) | KR100841182B1 (en) |
| CN (3) | CN1217576C (en) |
| AR (1) | AR030496A1 (en) |
| AU (2) | AU1816102A (en) |
| BR (1) | BRPI0113924B1 (en) |
| CA (1) | CA2422582C (en) |
| DE (1) | DE10046265A1 (en) |
| MX (1) | MXPA03002334A (en) |
| NZ (1) | NZ524752A (en) |
| PL (2) | PL360546A1 (en) |
| TW (1) | TWI241161B (en) |
| WO (1) | WO2002023985A2 (en) |
| ZA (1) | ZA200302153B (en) |
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| ES2392966T3 (en) * | 2002-07-26 | 2012-12-17 | Microban Products Company | Durable Antimicrobial Leather |
| AU2004201059B2 (en) * | 2003-03-26 | 2009-06-04 | Rohm And Haas Company | Microbicidal composition |
| DE10318366A1 (en) * | 2003-04-23 | 2004-12-02 | Bayer Chemicals Ag | Microbicidal agents |
| ATE435307T1 (en) * | 2005-03-04 | 2009-07-15 | Buckman Labor Inc | FUNGICIDE AGENTS AND METHODS USING CYANODITHIOCARBAMATES |
| CN100381052C (en) * | 2006-05-13 | 2008-04-16 | 林贤荣 | Antiseptic and mite-proof agent for mattress(sofa) |
| DE102008038709A1 (en) | 2008-08-12 | 2010-02-18 | Lanxess Deutschland Gmbh | Liquid preparations of phenolic drugs |
| US9997007B2 (en) * | 2009-10-01 | 2018-06-12 | Patent Investment & Licensing Company | Method and system for implementing mystery bonus in place of base game results on gaming machine |
| JP5604094B2 (en) * | 2009-12-17 | 2014-10-08 | 地方独立行政法人東京都立産業技術研究センター | Antifungal composition, and wood and wood products using the same |
| CN101864702B (en) * | 2010-05-26 | 2011-07-20 | 广东省石油化工研究院 | Papermaking sterilization preservative |
| EP2570502A1 (en) | 2011-09-13 | 2013-03-20 | LANXESS Deutschland GmbH | Liquid preparations for fungicidal protection of substrates containing collagen fibres |
| EP2777396A1 (en) | 2013-03-12 | 2014-09-17 | LANXESS Deutschland GmbH | Preparations for fungicidal protection of substrates containing collagen fibre |
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-
2000
- 2000-09-19 DE DE10046265A patent/DE10046265A1/en not_active Withdrawn
-
2001
- 2001-08-27 AR ARP010104081A patent/AR030496A1/en unknown
- 2001-09-07 PL PL36054601A patent/PL360546A1/en not_active IP Right Cessation
- 2001-09-07 CN CN018159141A patent/CN1217576C/en not_active Expired - Lifetime
- 2001-09-07 MX MXPA03002334A patent/MXPA03002334A/en active IP Right Grant
- 2001-09-07 AU AU1816102A patent/AU1816102A/en active Pending
- 2001-09-07 BR BRPI0113924A patent/BRPI0113924B1/en active IP Right Grant
- 2001-09-07 AU AU2002218161A patent/AU2002218161B2/en not_active Expired
- 2001-09-07 EP EP01985227.6A patent/EP1328155B1/en not_active Expired - Lifetime
- 2001-09-07 JP JP2002528033A patent/JP2004509137A/en active Pending
- 2001-09-07 NZ NZ524752A patent/NZ524752A/en not_active IP Right Cessation
- 2001-09-07 PL PL386766A patent/PL209118B1/en unknown
- 2001-09-07 CN CNA2005100819536A patent/CN1701664A/en active Pending
- 2001-09-07 CN CNA2006101002264A patent/CN1891043A/en active Pending
- 2001-09-07 WO PCT/EP2001/010303 patent/WO2002023985A2/en active IP Right Grant
- 2001-09-07 CA CA2422582A patent/CA2422582C/en not_active Expired - Fee Related
- 2001-09-07 KR KR1020037003883A patent/KR100841182B1/en active IP Right Grant
- 2001-09-13 US US09/952,252 patent/US7201854B2/en not_active Expired - Fee Related
- 2001-09-19 TW TW090122953A patent/TWI241161B/en not_active IP Right Cessation
-
2003
- 2003-03-18 ZA ZA200302153A patent/ZA200302153B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004509137A (en) | 2004-03-25 |
| KR100841182B1 (en) | 2008-06-24 |
| US7201854B2 (en) | 2007-04-10 |
| DE10046265A1 (en) | 2002-03-28 |
| WO2002023985A2 (en) | 2002-03-28 |
| CN1217576C (en) | 2005-09-07 |
| NZ524752A (en) | 2005-09-30 |
| CA2422582A1 (en) | 2003-03-14 |
| AR030496A1 (en) | 2003-08-20 |
| PL209118B1 (en) | 2011-07-29 |
| CN1460001A (en) | 2003-12-03 |
| MXPA03002334A (en) | 2003-10-15 |
| BR0113924A (en) | 2003-07-29 |
| EP1328155A2 (en) | 2003-07-23 |
| CN1701664A (en) | 2005-11-30 |
| CN1891043A (en) | 2007-01-10 |
| TWI241161B (en) | 2005-10-11 |
| US20020066879A1 (en) | 2002-06-06 |
| BRPI0113924B1 (en) | 2016-07-26 |
| AU2002218161B2 (en) | 2007-05-17 |
| EP1328155B1 (en) | 2016-04-27 |
| PL360546A1 (en) | 2004-09-06 |
| WO2002023985A3 (en) | 2002-10-24 |
| AU1816102A (en) | 2002-04-02 |
| KR20030032039A (en) | 2003-04-23 |
| ZA200302153B (en) | 2004-05-25 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20150908 |